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CN1318397C - 支链表面活性剂的制备 - Google Patents

支链表面活性剂的制备 Download PDF

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CN1318397C
CN1318397C CNB011244135A CN01124413A CN1318397C CN 1318397 C CN1318397 C CN 1318397C CN B011244135 A CNB011244135 A CN B011244135A CN 01124413 A CN01124413 A CN 01124413A CN 1318397 C CN1318397 C CN 1318397C
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branched
alcohol
preparation
chain acyl
alkyl
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CN1358710A (zh
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D·S·康纳
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Procter and Gamble Ltd
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Procter and Gamble Ltd
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    • C11D3/124—Silicon containing, e.g. silica, silex, quartz or glass beads
    • C11D3/1246—Silicates, e.g. diatomaceous earth
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    • A—HUMAN NECESSITIES
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    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/46—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing sulfur
    • A61K8/463—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing sulfur containing sulfuric acid derivatives, e.g. sodium lauryl sulfate
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    • C07C2/06—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms by addition between unsaturated hydrocarbons by oligomerisation of well-defined unsaturated hydrocarbons without ring formation of alkenes, i.e. acyclic hydrocarbons having only one carbon-to-carbon double bond
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    • C07C303/24—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of esters of sulfuric acids
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Abstract

使α-烯烃二聚形成亚乙烯基烯烃，然后将其异构化，并在羰基合成条件下将其与CO/H2反应或直接在羰基合成条件下与CO/H2反应，得到中链或接近中链支化的醇。这些支链醇是制备烷基硫酸盐、烷基乙氧基硫酸盐和烷基羧酸盐表面活性剂和其它表面活性剂的原料。

Description

支链表面活性剂的制备
本申请是申请号为97195560.3、申请日为1997年4月16日、发明名称为“支链表面活性剂的制备”的发明专利申请的分案申请。
发明领域
本发明涉及制备洗涤表面活性剂，特别是那些含有支链疏水单元的洗涤表面活性剂的方法。
发明背景
常规洗涤表面活性剂含有水增溶取代基(亲水基)和亲油取代基(疏水基)的分子。这类表面活性剂一般含有如羧酸盐、硫酸盐、磺酸盐、氧化胺、聚氧乙烯等亲水基，其连接在通常含有约10～约20个碳原子的烷基、烯烃基或烷芳基疏水物上。因此，这类表面活性剂的制造商必须能获得疏水基源，通过化学方法，可将所期望的亲水物连接到其上。最早的疏水基源包括天然脂肪和油，其可通过用碱皂化转化为皂(即羧酸盐亲水物)。椰子油、棕榈油仍可用来制备皂和制备烷基硫酸盐(“AS”)类的表面活性剂。其它疏水物可从石油化学品得到，其包括用来制备烷基苯磺酸盐表面活性剂(“LAS”)的烷基化苯。
文献称某些支链疏水物可被有利地用于制备烷基硫酸盐洗涤表面活性剂；例如，参考1969年11月25日授权给deWitt等人的美国专利3,480,556。但已确定，描述于‘556专利中的β支链表面活性剂在某种溶度参数方面是差的，如其克拉夫特(Krafft)温度所证实的那样。还进一步确定，支链朝向疏水物碳链中心的表面活性剂有很低的克拉夫特温度。参考：R.G.Lāughlin的“表面活性剂的水相性质”，学术出版社(“The Aqueous Phase Behavior of Surfactants”，AcademicPress)，纽约，1994年，第347页。因此，现已确定，这类表面活性剂特别优选用于冷水或低温水的洗涤条件(如20℃～5℃)。
制备具有中链或接近中链支化的疏水基的洗涤表面活性剂的一个相关问题是缺少这类疏水物的备用源。依据本发明，描述了一种制备这类支链疏水物和将其转化为中链或接近中链支化的表面活性剂的方法。
发明概述
本发明包括一种制备中链或接近中链支化的烯烃(主要是，在中链或接近中链区支化的甲基)的方法。然后将这类物质用作提供支链洗涤表面活性剂疏水部分的基本原料。
通过以下述反应序列说明本发明的方法．
1)α-烯烃的二聚
和
其中，R和R’为相同或不同的直链烷基，和其中R为C3～C7，优选为C5～C7的直链烷基，R’为C3～C7，优选为C5～C7的直链烷基。为了用于制备用于洗涤产品如洗衣用洗涤剂、洗餐具液体等的表面活性剂，R和R1优选相同或链长彼此在一或两个碳原子之内。有些直链烯烃还可由二聚作用制得，并可任选地被用分子筛除去。设计本发明方法的步骤1，以提供优选总计包含约12～约18(平均)个碳原子的支烯烃。
2)醇的制备
在步骤2(路线A)中，可将步骤1的烯烃混合物预先无规则化，以促进随后步骤3中醇(i)和醇(ii)的最终形成。可供选择地(步骤2，路线B)，可略去该预先无规则化步骤，羰基合成催化剂本身可在三个可能的末端位置上无规则化终产物。
路线A
Figure C0112441300054
或
路线B
制备醇的羰基合成方法被详述于Kirk-Othmer的 《化学工艺百科 全书》( Encyclopedia of Chemical Technology)第4版，第1卷，第903～8页，执行编辑：Jacqueline I.Kroschwitz，由纽约Wiley-Interscience出版。该步的催化剂为例如钴-一氧化碳-有机膦。
本方法步骤(2)的醇混合物包括用于如下步骤(3)的下述化学式的支链伯醇化合物。
和
Figure C0112441300063
和
少量的
Figure C0112441300064
要知道，当在R或R’位置取代CH2OH时，主要发生在其各自的末端碳，或在更小程度上，发生在其倒数第二个碳上。期望步骤(3)中存在最少量的化学式为(iii)的化合物。
3)表面活性剂的制备
有利地，本方法不导致成对支链化，即，无“季”碳取代。使用钴-一氧化碳物-有机膦时，位阻将阻止向亚乙烯基碳的逆向加成，否则将会形成非生物可降解的季碳。而且，几乎不(低于约3％)发生邻位支链化。当然，全部原料中仍有一些未被支链化。一般而言，优选从洗涤性能和生物降解性能的观点看，本方法在异构体i)和ii)情况下提供了具有一个靠近中心甲基的疏水物。
除非特别注明，本发明的所有百分比、比率和比例均以重量计。本发明引用的所有文献的相关部分均引入本发明作为参考。
发明详述
1)烯烃的二聚：
本发明包括由两个相同或接近相同链长的α-烯烃的二聚作用，以制成洗涤剂范围的亚乙烯基烯烃来制备表面活性剂前体疏水物的方法。这些C5～C10，优选C7～C9的α-烯烃被二聚得到C10～C20，优选C14～C18的亚乙烯基烯烃，经过羰基合成反应其可生成C11～C21，优选C15～C19的醇。有许多实现所述二聚作用的方法，参考美国专利申请9,200,398、美国专利4,658,078和美国专利4,973,788；O.S.Vostrikova，A.G.Ibragimov，G.A.Tolstikov，L.M.Zelenova和U.M.Dzhemilev著，Izv.Akad.Nauk SSSR，Ser.khim.，1980年第10期，第2330-2页[化学文摘94:65032]；日本公开特许公报06228016 A2[化学文摘122:186930]。
2)醇的制备
路线A
a部分)，用一种方法，如Shell在其SHOP方法中使用的异构化α-烯烃的方法，将亚乙烯基烯烃的碳碳双键预先异构化；参考《 Kirk-Othmer化学工艺百科全书》( Kirk-Othmer Encyclopedia of Chemical Technology)，第4版，第17卷，第848-50页，执行编辑：Jacqueline I.Kroschwitz，由纽约Wiley-Interscience出版，和《 化学经济学手册》( Chemical Economics Handbook)第681页，5053K-L，斯坦福研究所(Stanford Research Institute)，Menlo公园，加州94025，1993年10月。
b部分)用羰基合成化学将预异构化的亚乙烯基烯烃(现大部分为内烯烃)转化为伯醇混合物。为此，需要羰基合成催化剂，该催化剂在羰基化作用前将双键异构到α位，就象在一步法中使用羰基钴-膦催化剂一样，参考《 Kirk-Othmer化学工艺百科全书》( Kirk-Othmer Encyclopedia of Chemical Technology)第4版，第1卷，第903-8页(1991年)。采用路线A(包括预异构化作用)，以保证醇i和ii相对醇iii有相对高的产率。注意，i和ii的醇硫酸盐为所期望的表面活性剂，而iii的醇硫酸盐则是不足的。
路线B
该步骤直接对预先不异构化的亚乙烯基烯烃使用相同的羰基合成催化剂。这取决于催化剂在羰基化作用前，可彻底异构化亚乙烯基烯烃的碳碳双键。目的是相对iii而言，获得与路线A同样多的i和ii。
还可制备其它衍生于脂肪醇的表面活性剂，例如，烷基乙氧基硫酸盐(AES)、烷基多苷(APG)等。注意，除醇硫酸盐或AES以外的表面活性剂可由氧化所述醇或其醛中间体生成羧酸盐(即，一种支链皂)制得。该皂本身可为出色的表面活性剂和/或洗涤剂助剂。该羧酸盐还可被用作原料，并可用本领域公开的技术转化为支链酰基牛磺酸盐、酰基羟乙磺酸盐、酰基肌氨酸盐、酰基-N-甲基葡糖胺或其它酰基衍生的表面活性剂。
工业适用性
由本方法制得的支链型表面活性剂可被用于所有种类的洗涤组合物。这些组合物包括，但不局限于，粒状、条状和液态洗衣洗涤剂；液态手洗洗餐具组合物；液态、凝胶状和条状的个人洗涤用品；洗发香波；牙膏；硬表面清洗剂等。这些组合物可包含各种常规的洗涤组分。下文列出的这些组分可给配方设计者提供方便，并非借此限制可与本发明支链表面活性剂混合使用的组分类型。
本发明的支链表面活性剂可与洗涤助洗剂结合使用。这类助洗剂包括，例如，1～10微米的沸石A，多羧酸盐助洗剂，如柠檬酸盐，层状硅酸盐助洗剂，如“SKS-6”(Hoechst)和磷酸盐物质，特别是三聚磷酸钠(“STPP”)。大多数洗衣洗涤剂一般包含至少约1％的助洗剂，更一般地，包含约5％～约80％的助洗剂或助洗剂混合物。
可将酶如蛋白酶、淀粉酶、脂肪酶、纤维素酶、过氧化物酶及其混合物用于含有支链表面活性剂的洗涤剂组合物中。一般的洗涤剂组合物包含约0.001％～约5％的商品酶。
洗涤剂组合物还可包含聚合的去污剂(SRA’s)。这类物质包括，例如，阴离子、阳离子和不带电荷的单体单元，特加是聚酯物质。该类型的优选物质包括低聚对苯二酸酯、磺化的基本上直链的酯低聚物，其包含一对苯二酰基和氧化烯氧基重复单元的骨架，和衍生于邻苯二甲酰基的磺化的末端部分。各种SPR’s被描述于，例如，美国专利4,968,451；4,711,730；4,721,580；4,702,857；4,877,896；5,415,807和其它的参考文献中。这类去污物质一般占成品洗涤剂组合物的约0.01％～约10％。
洗涤剂组合物还可任选包含含有一种漂白剂和一种或多种漂白活化剂的漂白组合物。若存在漂白剂如过碳酸盐或过硼酸盐(具体为过硼酸盐一水合物“PB1”)，则其用量一般为成品洗涤剂组合物的约1％～约30％。可以使用漂白活化剂如壬酰氧基苯磺酸盐(NOBS)和四乙酰基乙二胺(TAED)及其混合物，以提高如过硼酸盐和过碳酸盐物质的漂白活性。若存在漂白剂活化剂，则其量一般为包括漂白剂和漂白活化剂的漂白组合物的约0.1％～约60％。还可使用其它的如被称作“光活化”漂白剂(参考美国专利4,033,718)的漂白剂。磺化锌酞菁为特别优选的光活化漂白剂。
洗涤剂组合物还可包含粘土污垢去除剂/抗再沉积剂，如乙氧基化四亚乙基五胺；见美国专利4,597,898。这类物质一般为完全配制的洗衣洗涤剂的约0.01％～约10％。
洗涤剂组合物还可包含约0.1％～约7％的聚合分散剂，其在沸石和/或层状硅酸盐助洗剂存在下是特别有用的。本领域已经知道这类物质(见美国专利3,308,067)。这类物质包括丙烯酸盐/苹果酸(malic)基共聚物，如描述于欧洲专利193,360中的那些，和聚乙二醇(“PEG”)。
本发明的洗涤剂组合物还可包含各种增白剂、染料转移抑制剂(特别是N-乙烯基吡咯烷酮和N-乙烯基咪唑的聚合物)、抑泡剂(特别是聚硅氧烷)、螯合剂，如次氮基三乙酸盐、乙二胺二琥珀酸盐等。这类物质一般为完全配制的洗涤组合物的约0.5％～约10％(重量)。
而且，要知道以本发明的方法制备的支链表面活性剂可被单独用于洗涤组合物中，或与其它洗涤表面活性剂混合使用。一般情况下，为获得在各种使用条件下对各种污垢和污渍宽范围的洗涤效果，完全配制的洗涤组合物将包含各类表面活性剂的混合物。本发明支链表面活性剂的一个优点是其能被容易地与其它已知类型的表面活性剂结合配制的能力。可以一般以约1％-约55％(重量)的含量用于本发明的其它表面活性剂的非限定性实例包括不饱和硫酸盐，如油基硫酸盐、C10～C18烷基烷氧基硫酸盐(“AEXS”；特别是EO1～7乙氧基硫酸盐)、C10～C18烷基烷氧基羧酸盐(特别是EO1～5乙氧基羧酸盐)、C10～C18甘油醚、C10～C18烷基多苷及其相应的硫酸化聚葡糖苷，和C12～C18α-磺化的脂肪酸酯。也可使用非离子表面活性剂，如乙氧基化的C10～C18醇和烷基酚(例如，C10～C18EO(1～10))。若期望，还可将其它常规的表面活性剂，如C12～C18甜菜碱和磺基甜菜碱(“sultaines”)、C10～C18氧化胺等加入全部组合物中。还可使用C10～C18N-烷基多羟基脂肪酰胺。一般实例包括C12～C18N-甲基葡糖酰胺。见WO9，206，154。其它衍生于糖的表面活性剂包括N-烷氧基多羟基脂肪酰胺，如C10～C18N-(3-甲氧基丙基)葡糖酰胺。N-丙基到N-己基C12～C18葡糖酰胺可用于低发泡。也可使用C10～C20的常规皂。若期望高发泡，则可用支链C10～C16皂。常用于洗衣洗涤剂组合物的C10～C14烷基苯磺酸盐(LAS)可与本发明的支链表面活性剂混合使用。
下述实施例说明了根据本发明制备的支链表面活性剂在各种洗涤组合物中的应用，但并不试图局限于此。
                           实施例1
如下制备粒状洗衣洗涤剂。
                A       B        C
吹制粉末
沸石A          30.0    22.0    6.0
硫酸钠         19.0    5.0     7.0
聚丙烯酸盐
LAS            13.0    11.0    21.0
支链AS*        9.0     8.0     8.0
硅酸盐，钠盐   -       1.0     5.0
皂             -       -       2.0
碳酸盐，钠盐   8.0     16.0    20.0
喷于
C10～C18EO7    1.0    1.0    1.0
干添加剂
蛋白酶         1.0    1.0    1.0
脂肪酶         0.4    0.4    0.4
淀粉酶         0.1    0.1    0.1
纤维素酶       0.1    0.1    0.1
NOBS           -      6.1    4.5
PB1            1.0    5.0    6.0
硫酸钠         -      6.0    -
水及微量组分  ----------------余量--------------
*C12～C14甲基支化的烷基硫酸盐，按上文所公开的内容制备。
一种含漂白剂的非水液态洗衣洗涤剂制备如下：
                                实施例II
组分                        重量％     范围(重量％)
液相
支链AS*                    25.3      18～35
C12-14，EO5醇乙氧基化物    13.6      10～20
己二醇                     27.3      20～30
香料                       0.4       0-1.0
固体物
蛋白酶                     0.4       0～1.0
柠檬酸三钠，无水           4.3       3～6
过硼酸钠(PB-1)             3.4       2～7
壬酰氧基苯磺酸钠(NOBS)    8.0       2～12
碳酸钠                    13.9      5～20
二乙基三胺五乙酸(DTPA)    0.9       0～1.5
增白剂                    0.4       0～0.6
抑泡剂                    0.1       0～0.3
少量组分           ----------余量----------
*C12～C16甲基支化的烷基硫酸盐，钠盐，按上文所公开的内容制备。
一种手洗餐具液体如下：
                                   实施例III
组分                         ％(重量)     范围(重量％)
支链AS*                     13.0        5～15
C12～C13烷基乙氧基硫酸铵    15.0        10～35
椰子基氧化胺                2.6         2～5
甜菜碱**/Tetronic704_      0.87～0.10  0～2(混合物)
醇乙氧基化物C8E11           5.0         2～10
二甲苯磺酸铵                4.0         1～6
乙醇                        4.0         0～7
柠檬酸铵                    0.06        0～1.0
氯化镁                      3.3         0～4.0
氯化钙                      2.5         0～4.0
硫酸铵                      0.08        0～4.0
过氧化氢                    200ppm      0～300ppm
香料                        0.18        0～0.5
Maxatase_蛋白酶            0.50        0～1.0
水和少量组分           ----------余量----------
*C12C14甲基支化的烷基硫酸盐，三乙醇铵盐，按上文所公开的内容制备。
**椰子烷基甜菜碱。
综上所述，本发明提供了一种制备支链烷基硫酸盐的方法，其包括步骤：
(a)使化学式为RCH＝CH2和R’CH＝CH2的α-烯烃二聚，形成下式的烯烃：
Figure C0112441300131
和
Figure C0112441300132
其中，上述化学式中R和R’可为相同或不同的C3～C7直链烷基取代基；然后，或者
(b)将步骤(a)的烯烃异构化，随后使所述异构化的烯烃在羰基合成条件下与CO/H2反应；或直接使步骤(a)的烯烃在羰基合成条件下与CO/H2反应；和
(c)回收所期望的下式的支链醇：
Figure C0112441300133
和
Figure C0112441300134
及硫酸化所制备的醇。
一种制备支链烷基乙氧基硫酸盐的方法，其包括先将根据上述方法所制备的醇乙氧基化，然后硫酸化。
一种通过氧化根据上述方法所制备的醇或其醛中间体而制备支链烷基羧酸盐表面活性剂的方法。一种用根据此法所制备的支链羧酸盐作为原料，制备支链酰基牛磺酸盐、支链酰基羟乙磺酸盐、支链酰基肌氨酸盐或支链酰基N-甲基葡糖胺等的方法。

Claims (4)

1.一种制备支链烷基硫酸盐表面活性剂的方法，其包括步骤：
(a)使化学式为RCH＝CH2和R’CH＝CH2的α-烯烃二聚，形成下式的烯烃：
和
Figure C011244130002C2
其中，上述化学式中R和R’为相同或不同的C3～C7直链烷基取代基；然后，或者
(b)将步骤(a)的烯烃异构化，随后使所述异构化的烯烃在羰基合成条件下与CO/H2反应；或直接使步骤(a)的烯烃在羰基合成条件下与CO/H2反应；和
(c)回收所期望的下式的支链醇：
和
及硫酸化所制备的醇。
2.一种制备支链烷基乙氧基硫酸盐的方法，其包括
根据权利要求1的方法中的步骤制备醇，
还包括先将所述根据权利要求1的方法中的步骤制备的醇乙氧基化，然后硫酸化。
3.一种制备支链烷基羧酸盐表面活性剂的方法；其中
通过进行权利要求1的方法中的步骤制备醇，且通过氧化所述依据权利要求1的方法中的步骤所制备的醇，而制备支链烷基羧酸盐表面活性剂。
4.一种制备支链酰基牛磺酸盐、支链酰基羟乙磺酸盐、支链酰基肌氨酸盐或支链酰基N-甲基葡糖胺表面活性剂的方法；其特征在于：
以权利要求3的方法制备支链羧酸盐，
使用所述根据权利要求3的方法所制备的支链羧酸盐作为原料制备所述支链酰基牛磺酸盐、支链酰基羟乙磺酸盐、支链酰基肌氨酸盐或支链酰基N-甲基葡糖胺表面活性剂。
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CN1358710A (zh) 2002-07-17
MX9808555A (zh) 1999-02-28
ATE220389T1 (de) 2002-07-15
EP0900181B1 (en) 2002-07-10
MA24136A1 (fr) 1997-12-31
MA24137A1 (fr) 1997-12-31
ES2179342T3 (es) 2003-01-16
CN1106366C (zh) 2003-04-23
TR199802077T2 (xx) 1999-01-18
BR9708678A (pt) 1999-08-03
KR100307426B1 (ko) 2001-11-30
ZA973246B (en) 1997-11-14
EP0900181A1 (en) 1999-03-10
KR20000005563A (ko) 2000-01-25
US6326348B1 (en) 2001-12-04
DE69713887T2 (de) 2003-02-27
CZ334598A3 (cs) 1999-03-17
MX219947B (zh) 2004-04-16
US6015781A (en) 2000-01-18
US20010034461A1 (en) 2001-10-25
JPH11507957A (ja) 1999-07-13
US6133222A (en) 2000-10-17
CA2252435A1 (en) 1997-10-23
WO1997038957A1 (en) 1997-10-23
US6320080B2 (en) 2001-11-20
CA2252435C (en) 2004-03-23
DE69713887D1 (de) 2002-08-14
CN1222133A (zh) 1999-07-07
AU2991097A (en) 1997-11-07

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